Ivan gubelmann



Patented Dec. 27, 1927.

UNITED STATES PATENT OFFICE.

IVAN GUBELMANN, HENRY J. WETLAND, AND OTTO STALLMANN, OF SOUTH MILWAU- KEE, WISCONSIN, ASSIGNOBS TO THE NEWPORT COMPANY, 01 CARBOLLVILLE, WISCONSIN, A' CORPORATION OF DELAWARE.

3'-AMINO4'-HYDROXY-ORTHO-BENZOYL No Drawing.

This invention relates to 3-amino-4'-hydroxy-ortho-benzoyl benzoic acid and a process of making the same.

We have discovered that 3-amino-4-hy- 5 droxy-ortho-benzoyl benzoic acid can be prepared by the reduction ofthe corresponding nitro-hydroxy body. The general reaction may be expressed by the following chemical The method .of reduction used is similar to the general method of reducing nitro bodies with iron and dilute acids. However, we do not wish to limit our method to any specific reduction rocess, since these nitro bodies can be re uced by other methods, such as electrolytically, by hydrogen and a catalyst,-

by tinand hydrochloric acid, and the like.

3-amino-4'- ydro -ortho-be nzoyl benzoic acid is a pale ye low powder which apparently has no definite melting point, for

u on heatin it up in a capilla tube, it bens to deco orize at 260 C. an decompose.

en heated to 350 to 400 C., it decomposes to a black residue. The compound s practically insoluble in ordinary organic solvents and glacial acetic acid, but it IS easily soluble in dilute caustic soda solution,

'ving a yellow colored solution. It is solu-' 40 10 in an excess of dilute mineral acid. The

sulfate is sparing v and quite soluble in hot, which fact furnishes a method of recrystallization and purification. Y

48 Without limiting our invention to any particular procedure, the following example, in which parts by weight are given, illustrates the application 'of our invention in the preferred form:

To 300 parts of water are added 400 parts soluble in cold water- BENZOIC ACID AND PROCESS OF MAKING THE SAME.

Application filed June 28, 1926. Serial No. 119,249.

of iron dust and 37 parts of lacial acetic acid or an equivalent amount 0 dilute acetic acid. This mixture is then heated to 90 to 9? C. and a paste, prepared from 287 parts 0 zoic acid and 1200 parts of water, is added over a period of 2'to 3 hours. The reaction mass is held at 90-95 C. for 2 hours longer, at the end of which time the reduction is considered completed. A solution of 100 parts of soda ash in 500 parts of water is added to the reduction mass. The iron precipitate is then filtered off at 95 to 100 C. and the cake washed with 500 c. 0. water. The filtrate, including the wash water, is slowly run into a mix consisting of 250 parts of hydrochloric acid 20 Be. and 1000 parts of ice. The acidity of the resultin precipitated mass is ad'usted to a wea acidity toward methyl re paper by the addition of either acid or caustic soda. The precipit a te d' 3-amino-4'-hydroxy-ortho-benzoylbenzoic acid is now filtered off and dried at 100 0., a yield of 231 parts being obtained.

We are aware that numerous details of the process may be varied without de arting from the spirit of this invention, an we do not desire limiting the patent granted other than as necessitated by the prior art.

We claim as ourinvention:

As a new article of manufacture 3'-amino- 4'-hydroxy-ortho-benzoyl benzoic acid, having most probably the following formula:

NHI

In testimony whereof, we have hereunto subscribed our names.

IVAN GUBELMANN. mmmv J. WEILAND. o'rro s'rammm.

3'-nitro-4'-hyd roxy-ortho-benzoyl ben- 

